Ethanol → HCID 90302175, compound

HRID 2169689Notes

Reaction equation

HRID 2169689 reaction equation
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[CH3:31][C:32]1([CH3:66])[C:56]2[C:36]([CH:37]=[C:38]3[CH:55]=[C:54]4[C:41]([C:42]5[C:47]([C:48]6[C:53]4=[CH:52][CH:51]=[CH:50][CH:49]=6)=[CH:46][CH:45]=[CH:44][CH:43]=5)=[CH:40][C:39]3=2)=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33]1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C1(C)C=CC=CC=1>[CH3:66][C:32]1([CH3:31])[C:56]2[C:36]([CH:37]=[C:38]3[C:39]=2[CH:40]=[C:41]2[C:54]([C:53]4[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=4[C:47]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=42)=[CH:55]3)=[CH:35][C:34]([C:2]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[CH:18][CH:17]=3)=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)=[CH:33]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86727987HCID 86727987, compound

Product 1

HCID 90302175HCID 90302175, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6.5 g (14 mmol) of 2-(4-(10-bromoanthracen-9-yl)naphthalene-1-yl)thiophene, 7.53 g (16 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.16 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium, 11 ml of 2M Na2CO3, 30 ml of EtOH and 65 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 4 h. After finishing the reaction, the mixture was allowed to cool to room temperature. Than 500 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 6.4 g (yield 63%) of yellow product which was recrystallized from toluene. MS (m/z, FAB+): 728.1; 1H NMR (CDCl3, 400 MHz): chemical shift (ppm) 9.13 (s, 1H), 8.64˜8.56 (m, 3H), 8.31˜8.05 (m, 5H), 7.95˜7.83 (m, 9H), 7.68˜7.61 (m, 2H), 7.55 (d, J=8.00 Hz, 1H), 7.49˜7.40 (m, 6H), 7.18 (d, J=6.20 Hz, 1H), 7.02 (t, J=6.20 Hz, 1H), 6.55 (d, J=8.00 Hz, 1H), 1.81 (s, 6H).

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered off with suction

Sources & evidence

ORD record
ord-6e4ff6f228cb45ebb081ed6f844d93b6
Source dataset
uspto-grants-2015_06
Patent number
US09048437B2

Reaction notes

Loading…